反応 #595339

反応方程式

compound

Ethyl 2-iodo-1,3-oxazole-4-carboxylate

4-chloro-3-methylphenylboronic acid

cesium carbonate

→

Ethyl 2-(4-chloro-3-methylphenyl)-1,3-oxazole-4-carboxylate

溶媒

N-methyl-2-pyrrolidone

water

water

ethyl acetate

反応条件

後処理

1. 1
   温度The mixture is then cooled to RT
2. 2
   抽出The aqueous phase is extracted twice with in each case 20 ml of ethyl acetate
3. 3
   洗浄The combined organic phases are washed once with 10 ml of sat. aqueous sodium chloride solution
4. 4
   乾燥dried over magnesium sulfate
5. 5
   ろ過After filtration
6. 6
   その他the solvent is removed on a rotary evaporator
7. 7
   その他The residue is purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5)

実験手順

385 mg (1.44 mmol) of the compound from Example 25A and 319 mg (1.87 mmol) of 4-chloro-3-methylphenylboronic acid are initially charged in 12.7 ml of dry N-methyl-2-pyrrolidone. 105 mg (0.14 mmol) of bis(diphenylphosphino)ferrocenepalladium(II) chloride, 0.33 ml water and 940 mg (2.88 mmol) of cesium carbonate are then added. The reaction mixture is stirred at 50° C. for 4 h. The mixture is then cooled to RT, and 20 ml of ethyl acetate and 10 ml of water are added. The aqueous phase is extracted twice with in each case 20 ml of ethyl acetate. The combined organic phases are washed once with 10 ml of sat. aqueous sodium chloride solution and dried over magnesium sulfate. After filtration, the solvent is removed on a rotary evaporator. The residue is purified by preparative HPLC (column: YMC GEL ODS-AQ S-5/15 μm; mobile phase gradient: acetonitrile/water 10:90→95:5).

出典